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目的合成天然产物4-取代苯并口恶唑酮衍生物并对其抗炎镇痛活性进行初步评价。方法以2-氨基间苯二酚为原料,与三光气缩合制得4-羟基-苯并口恶唑酮;以2-取代苯酚为起始物,经取代、重排、氧化反应得到取代苯磺酰氯,取代磺酰氯与4-羟基-苯并口恶唑酮反应制得4-苯磺酰氧基-苯并口恶唑酮酯类化合物。采用二甲苯致小鼠耳肿胀法和小鼠醋酸扭体法测定目标化合物的抗炎及镇痛活性。结果与结论共合成了11个目标化合物,其中10个化合物未见文献报道,目标化合物的结构经ESI-MS、1H-NMR、13C-NMR谱确证;活性实验结果显示,化合物5g具有一定的抗炎活性,化合物5a、5d、5j具有较好的镇痛活性。
OBJECTIVE: To synthesize 4-substituted benzoxazolone derivatives as natural products and evaluate their anti-inflammatory and analgesic activities. Methods 2-Amino resorcinol was used as the raw material and condensed with triphosgene to obtain 4-hydroxy-benzoxazolone. The substituted 2-substituted phenol was used as a starting material to get substituted benzenesulfonamide by substitution, rearrangement and oxidation Acid chlorides and substituted sulfonyl chlorides react with 4-hydroxy-benzoxazolone to give 4-benzenesulfonyloxy-benzooxazolone esters. The anti-inflammatory and analgesic activities of the target compounds were determined using xylene-induced mouse ear swelling and mice acetic acid writhing assay. RESULTS AND CONCLUSIONS A total of 11 target compounds were synthesized, of which 10 compounds were not reported in the literature. The structures of target compounds were confirmed by ESI-MS, 1H-NMR and 13C-NMR spectra. The results of the activity tests showed that 5g Inflammatory activity, compounds 5a, 5d, 5j have better analgesic activity.